


Nathaniel Plimpton, III Falls For the First Time

by HisBeloved



Category: Crazy Ex-Girlfriend (TV)
Genre: Adderall Abuse, But he's not sure he dislikes it, College Student Nathaniel, F/M, First Love, First Relationship, Harry Potter related sex acts, Learning About Sex, Nataniel gets used for his body, Sexual Experimentation, Stanford University, University
Language: English
Status: Completed
Published: 2020-02-22
Updated: 2020-02-22
Packaged: 2021-02-27 20:02:04
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,084
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22851442
Author URL: https://archiveofourown.org/users/HisBeloved/pseuds/HisBeloved
Summary: This is a short story about the first girl Nathaniel Plimpton fell hard for. Maybe I'll do Mona next?
Relationships: Nathaniel Plimpton/Original Female Character(s)
Comments: 2
Kudos: 8





	Nathaniel Plimpton, III Falls For the First Time

**Author's Note:**

> I love Crazy Ex-Girlfriend and I'm Team Nathaniel. I love Greg, but ultimately I think Nathaniel and Rebecca are more suited for each other and just damn hot together. Anyhoo, I started thinking one day about the women in his life. Who was it that turned him into such a sexy beast? Leah Dershowitz was born.
> 
> Trigger warning for implied Adderall abuse.

Her name had been Leah Dershowitz (‘yeah, those Derchowitz’s,’ she’d said rolling her eyes when his eyes must have shown his appreciation). She had sarcastically told him at their first meeting, back in Freshman year during orientation, that she was a typical New York Jewish American Princess. In Sophomore year, when Toby Shriver (yeah, those Shriver’s) had called her a JAP she’d punched him so hard that he’d actually needed a root canal. The same year that she was the Financial Officer of the Stanford Pre-Law Society and pulling a 4.0 as an International Relations major. 

Nathaniel Plimpton, II had recently told him that he’d read in the alumni journal that she’d landed a job as an SFO at The Brookings Institute. He’d been impressed. He’d always liked Leah. Everyone had.

She was hotter than fiendfyre, burning every man that she came into contact with to ash. She was a Slytherclaw, more Claw than Slyther. She was one of the most brilliant women that he had ever met up to that point and she wasn’t above using her considerable powers of persuasion to get what she wanted. She had spotless olive toned skin (well, except for that wonderful freckle that had been – well, men don’t talk, do they?), a thick head of straight hair so black that it had almost blue highlights (just like Diana Prince in all of his old comic books), and curves in all the right places. God, her ass. He still sometimes finds himself thinking about her ass. Her eyes were brown; she hadn’t liked them; had worn green contacts for a while. But when you got lucky enough to get close to Leah, when you got the opportunity to really examine her deep, dark irises, you saw that they were flecked with amber and green and the smallest slivers of blue. Her lips were lush and full, the most alluring shade of pink with just the littlest bit of brown. He had loved watching her put her MAC lip gloss on them, dabbing the edges of her lips with her pinkie finger (right at the table! Mother would have been scandalized) after she’d eaten.

The first time he’d kissed her it was at a party on the Row where she had him backed into a corner, a fifth of vodka in her hand despite Stanford’s strict alcohol policy, trying to teach him about Nietzsche, nihilism, and bragging about how she’d successfully written an entire paper in Intro to Statistical Methods using Wikipedia as her primary source. She’d been looking somewhere over his head, saying something about the Myers Briggs Inventory, and all he could focus on were her lips. And how he didn’t want to die without finding out what they tasted like. So he’d kissed her.

Her lips were sticky and had tasted like alcohol. But they hadn’t stayed sticky for long because as soon as she’d gotten over the shock that his mouth was on hers she’d started kissing him back and they hadn’t left that corner for the rest of the party. He’d never kissed anyone like he’d kissed Leah and he’d never known a girl who could use her tongue like that. He’d never known a girl who knew exactly where to put her leg and exactly when to put it there to draw noises that were so obscene out of him that, had he not been temporarily unable to think, he’d have been mortified to hear himself make in public. When he’d finally gotten out of that corner, as he’d walked her back to her apartment, she’d pushed him against a tree once and he’d pushed her against a building twice before they’d even reached her door. When she was looking for her keys he knew that she would have let him come in with her. She hadn’t been drunk, and god knows how she’d managed that, but he’d been too much of a gentleman. But he hadn’t left without kissing her for what felt like hours, their bodies melded from head to pelvis, humping each other until they’d both almost come multiple times. He’d had to walk around the campus for 45 minutes before his erection had gone away (his pants hadn’t done anything to hide it). When he’d finally looked in the mirror that night, he’d been shocked at the state of his hair – he looked like he belonged in some teenage boy band it was so unkempt. No wonder that guy that he’d seen at the LGBTQ table every week in the cafe and knew full well that he was straight had propositioned him. Even he knew that he had looked good enough to eat.

There was lots of late night humping after that, but Leah had closed the door to sex. She’d told him that she’d never been turned down before and she had to make him pay. No girl had ever said anything like that to him and it had gone straight to his cock. Right after that, she’d thrust so hard into him that he’d come in his pants harder than he ever remembered coming. He had momentarily been terrified that he’d gone blind. She continued to make out with him after that, not caring about the mess in his pants. She’d said it was hot.

He started to go on dates with her, to take her out to dinner, to the movies, to coffee shops and book stores. After a while it became less about getting into her pants and more about getting to know her underneath all her non-stop political analysis and pop culture commentary. At Barnes and Noble they’d shared a set of head phones and she’d sang Disco Stick to him while fluttering angelic eyelashes at him, a smirk full of sin and hedonism on her lips. He’d had to convince himself that the Barnes and Noble men’s room was not an appropriate place to jack off, no matter how horny your cock-blocking, insatiable girlfriend made you. The same day she’d told him about her brother’s multiple heroin overdoses, about how they couldn’t get him sober, about how her father had cut him off because he’d run out of ways to control him. She was afraid that he would die before she’d ever have the opportunity to tell him how much she loved him, how much she missed what it had been like when they were kids, just them against the world. He’d never had a girl open up to him like that before and he was afraid of the power that it gave him.

She came to every one of his home water polo games with some of the girls in her sorority. Wore a Stanford Water Polo shirt and put read and white stripes on her cheeks and he could always hear her cheering for him over the splash of the water and the shouts and grunts of the men around him. She told him that he looked like Francis Ford Coppola’s Dracula in his bonnet and he’d chased her around the lawn outside of the Aquatic Center before tackling her and tickling her until she called “uncle.”

He’d had sex a few times before; they had all been unmitigated disasters. The most notable time had been in his senior year of prep school. The girl, Carrie, had been alright, he’d even liked her, thought she was funny, thought she wouldn’t be bad to hang around with. But it had been at a house party in Laguna and there hadn’t been enough bedrooms and they couldn’t get the door to lock and every time the door would open he’d lose it and they’d have to start over again. When he’d finally entered her, he’d almost come so many times already that he came instantly. Fortunately, Carrie wasn’t a gossip, so she didn’t tell everyone about his massive failure. And she’d showed him how to finger her until she came so all in all she’d been happy.

He was a hyper-focused student his freshman year. He’d forgone much of a social life to end the year with a 3.98 grade point; it was those 0.02 points that had gotten him to loosen up a little so that by the time sophomore year rolled around he’d found himself backed up into a corner at a party on the Row with Leah Dershowitz cramming her leg between his.

When it finally happened, the day hadn’t been notable in any way. She had come over to his dorm room with her Poli Sci text book and deposited herself in his desk chair, watching him over her book while he worked on a paper about American Colonialism. One minute he was typing something about the true principles of natural religion and the next moment a roll of condoms was being tossed onto his keyboard and Leah’s Poli Sci text was nowhere to be seen.

Not very long after that, they were both in their underwear and Leah was running her hands over his abs looking like she wanted to lick him from head to toe. The next minute he realized that licking Leah from head to toe sounded like a good idea and before he knew it he found himself licking a long stripe from the waistband of her hot pink Victoria’s Secret panties right up over her matching bra, between the valley of her not inconsiderable breasts all the way to the bottom of her chin. Leah didn’t cuss a lot, she thought it made a person look ignorant, so he knew that he was doing something right when she gasped ‘fuck’ as he put his hand into her panties.

He learned that day that there were a lot of ways to get Leah to cuss, you just had to know which buttons to push. She liked it when he flicked his tongue over her clit, liked to have her nipples pinched, loved it when he barely kissed a spot right behind her right ear, said ‘shit’ when he licked the tiny mole on her perineum, and he got a ‘mother fucking Jesus fucking Christ’ when he crooked two fingers into her and discovered that bumpy swollen area just inside of her and pulsed his fingers against it again and again until her voice went scratchy and she shouted as her legs flew together and she arched off of the bed away from him, looking at him like he was God and Jesus and Mary all at the same time.

He learned that one advantage to being cock-blocked by your hot as hell girlfriend was that you masturbated constantly, and masturbating constantly increases your endurance, and that when you have a hot as hell girlfriend who orgasms over and over again when you finally get to have sex with her that endurance is a wonderful thing. He had never had a girl look like that underneath of him, like she was about to leave her body and come back to life all at the same time. He had never had a girl grab at him like she would die if he didn’t get deeper _now_ and leave scratch marks that he would feel three days later on his ass.

He’d had to buy waterproof concealer to hide the scratches that weren’t concealed by his Speedo. She’d _really_ liked that.

He fell for her. Hard. He’d taken her home to meet his parents and, while he’d been terrified that they would reject her for being Jewish, he’d found that he had nothing to worry about. She had held Nathaniel Plimpton, II in the palm of her hand, had even spoken about being a Democrat without so much as a flinch from his father. 

He was in complete, total awe of her.

He learned about sex from her. He became addicted to finding new ways to make her moan, day dreamed about making her come, watched ridiculous amounts of porn to learn new ways to make her scream until her voice gave out. She let him experiment on her, let him shower with her and get down between her legs and get a good look at her pussy, tried every position that they could manage from the Cosmo Position a Day desk calendar that she kept hidden in her bathroom closet behind the towels. She dressed up as Pansy Parkinson for him and he used her Slytherin scarf to tie her hands to her headboard while he fucked her with abandon, getting more and more worked up every time she called him Draco, coming with a shout after she squirted all over him, surprising both of them.

To say that she only got more aggressive after that was an understatement. They were having so much sex that he was having trouble getting his school work done, had actually skipped a few classes, and was screamed at by his water polo captain for being half asleep at too many practices. His advisor had pulled him aside and asked him if he had started doing drugs because he’d noticed that his A’s were turning into A-‘s. 

All the while she remained as brilliant as ever, participating in philanthropy events with her sorority, taking more hours than was sane, even publishing in a literary journal so that she would have something else to add to her CV. 

There was also the question of her feelings toward him. Every time he tried to broach the subject she expertly steered the conversation to something else entirely. When he bought her thoughtful gifts, she seemed appreciative but somehow less than enthused. He started to get the feeling that she was using him for his body – well, his dick specifically. She seemed to thrive off of sex, so much so that he’d spent an evening seriously considering whether she could be a succubus, slowly robbing him of his youth and vitality, his very soul.

She was the greatest woman he had ever known, he could write sonnets just about the curve of her hips, but she was exhausting.

Plimptons never say die, never admit defeat, so he held on to her. He bought a Keurig with an eight-cup coffee pot and Red Bull and 5-Hour Energy to keep up with her. He missed lunches to get assignments done, did extra weight sessions to maintain his athletic edge. He started using that concealer that he’d bought for his ass to hide the circles under his eyes and had to invest in facials when the stress started making his skin break out. He had a basket full of skin care creams and another full of multivitamins and performance enhancers and some surreptitiously obtained Adderall hidden on the top shelf of his closet.

He thinks it was the basket of pill that had started the downward spiral. She had been looking for a shirt to borrow in his closet when she came across his basket and stared at it for a worryingly long amount of time, her face devoid of all emotion. The Adderall certainly didn’t help matters; she laid into him about how dangerous it was to buy illegal prescriptions, about how he didn’t even know what was in the capsules, that he could get addicted to it and she wasn’t going to have anything to do with an addict. Screamed about how her brother wasn’t ever going to be the same, about how his addiction had started innocently enough with Nyquil, before flushing the entire bottle of Adderall down the toilet as he screamed back at her that if she wasn’t around he wouldn’t need it, how she was sucking the life out of him, how Nathaniel Plimpton, II had come down on him for his grades falling and how his performance was shit during matches.

They’d never had a fight before and it turned out that they couldn’t come back from the only one they’d had. She didn’t trust him and insisted on checking his room for illicit substances every time that she came over, always unannounced at all hours of the day and night. He started to go over to her apartment less and less and noticed that he felt better, that his classes started getting easier and his team mates had started to respect him again in the water. He realized that he’d neglected friendships and started hanging out with his friends more and more. One day he didn’t call her and she didn’t call him. A month later they were officially Facebook single.

They had always remained friendly toward one another. They’d even hooked up twice after the break-up, when they’d both been lonely and horny and wanted a good lay. Both times were criminally magnificent. He’s pretty sure that some of the things that they’d done to each other during those hook-ups were still crimes in some parts of the United States. She’d somehow procured a sex swing between the first and second hook-up and, well, a gentleman doesn’t talk, does he?

The last time he’d seen her had been right before he’d moved to West Covina. They’d run into each other at Barnes and Noble, of all places. She had been reading the back of a book on Environmental Policy when he’d seen her. She looked as flawless and terrifyingly beautiful as she had been at Stanford. She had also been very, very pregnant. He’d watched while a tall man with curly, sandy blond hair had brought her a Vanilla Bean Crème and kissed her behind her ear on the spot that he’d discovered that first time with her. He’d felt unbearably lonely in that moment and left before she could see him.

It had not been one of his better evenings.

A month later he walked into the offices of Whitefeather & Associates, the motliest crew of lawyers and paralegals that he had ever had the displeasure of laying his eyes on. A law office whose star lawyer, the entire reason his father had invested in the firm, apparently came and went whenever she pleased and finally decided to show up at the office in a wet suit with her Neanderthal boyfriend spouting off something about raging waters and amusingly threatening to quit. Later that week she’d jumped him and tried to stab him. She was a lunatic who also happened to be brilliant and loyal and had beautiful eyes and a not inconsiderable set of breasts.

Her name was Rebecca Bunch. He knew from the first moment that he saw her that he was a goner.


End file.
